In a Bromination Reaction, which of these reactions would react the fastest and

Question

In a Bromination Reaction, which of these reactions would react the fastest and WHY? Please explain in detail in terms of resonance structures, Pi bonds and ect.

The Arenes being reacted with Bromine are: benzhydrol, diphenyl ether, Terepthalic acid, Phenol, Anisole. List them from fastest to slowest please with the explanation.

Thanks!

Explanation / Answer

Order (in highest to lowest rate) benzhydrol (two aeromatic ring and one free ocygen lone-pair) > diphenyl ether (two aeromatic ring but here lone pair is in resonance so is not free) > Terepthalic acid ( one aeromatic ring and two oxygen with free lone-pair ) >Anisol ( one aeromatic ring and -CH3 group) > Phenol (one aeromatic ring) Bromaination is favoured by hight electron density.

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